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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Dynamic Equilibrium02:20

Dynamic Equilibrium

A reversible chemical reaction represents a chemical process that proceeds in both forward (left to right) and reverse (right to left) directions. When the rates of the forward and reverse reactions are equal, the concentrations of the reactant and product species remain constant over time and the system is at equilibrium. A special double arrow is used to emphasize the reversible nature of the reaction. The relative concentrations of reactants and products in equilibrium systems vary greatly;...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

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Related Experiment Video

Updated: May 25, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Dynamic imine chemistry.

Matthew E Belowich1, J Fraser Stoddart

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.

Chemical Society Reviews
|February 8, 2012
PubMed
Summary
This summary is machine-generated.

Dynamic covalent chemistry utilizes reversible imine bonds for constructing complex molecules and materials. This thermodynamic control offers error-checking and access to novel structures not achievable with traditional kinetic methods.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Last Updated: May 25, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Imine bond formation from amines and aldehydes is a reversible reaction governed by thermodynamic control.
  • Dynamic covalent chemistry (DCC) leverages reversible reactions for constructing complex molecular architectures.
  • DCC offers advantages over supramolecular chemistry by forming robust covalent bonds instead of noncovalent interactions.

Purpose of the Study:

  • To review the application of dynamic imine bonds in constructing molecules and materials.
  • To highlight the role of thermodynamic control in synthetic chemistry.
  • To showcase the construction of mechanically-interlocked molecules and novel materials using DCC.

Main Methods:

  • Utilizing reversible imine bond formation under thermodynamic control.
  • Employing template-directed protocols to preorganize molecular building blocks.
  • Applying DCC for the synthesis of complex structures like rotaxanes, catenanes, and knots.

Main Results:

  • DCC enables the synthesis of thermodynamically stable products through inherent 'proof-reading' mechanisms.
  • Reversible imine bonds facilitate the construction of highly symmetrical molecules and extended structures.
  • Template-directed DCC provides precise control over topology and the formation of mechanically-interlocked molecules.

Conclusions:

  • Dynamic imine bonds are versatile tools in DCC for creating advanced molecular structures and materials.
  • Thermodynamic control in synthesis opens new avenues in chemical topology and materials accessibility.
  • DCC offers a powerful and adaptable approach to modern synthetic challenges.